Destinations
Cuba
Time-stopped Havana, cobalt Caribbean keys, and a country on the edge of change.
Season
November - April for dry weather
Terrain
ocean
Fly into
HAV / SCU
Missions
1
The briefing
Cuba is a destination that will not stay as it is. The combination of preserved Spanish colonial architecture, 1950s American car culture, Caribbean coastline, and revolutionary mountain wilderness is a window that is slowly narrowing. Havana is unmissable - the Malecón at dusk, the crumbling Habana Vieja lanes, the salsa bars where the music genuinely doesn't stop. Book the scarce piece first in Cuba; everything else can wait a week.
Havana is unmissable - the Malecón at dusk, the crumbling Habana Vieja lanes, the salsa bars where the music genuinely doesn't stop. But the country rewards moving: Viñales' tobacco valley, Trinidad's time-capsule streets, and the eastern Sierra Maestra's hiking trails.
Travel logistics require flexibility. Internet access is limited, ATMs are unreliable, and plans change with the weather and the infrastructure. These are not problems - they are the character of the place.
How to get there
Gateway airports: HAV, SCU. Build the rest of the trip around the arrival.
Book first
Flights - HAV → Stay on the coast so the days never include a transfer in Cuba → Operator - ferry or boat once the nights are locked
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Missions in Cuba